64187-42-4

Basic information

• Product Name: N-CARBOBENZOXY-L-PHENYLALANINE VINYL ESTER
• Synonyms: L-Phenylalanine, N-((phenylmethoxy)carbonyl)-, ethenyl ester; Alanine, N-benzyloxycarbonyl-3-phenyl-, vinyl ester, L-; Alanine, N-carboxy-3-phenyl-, N-benzyl 1-vinyl ester, L-; L-N-Carboxy-3-phenylalanine N-benzyl 1-vinyl ester; N-((Phenylmethoxy)carbonyl)-L-phenylalanine ethenyl ester; N-Benzyloxycarbonyl-L-phenylalanine vinyl ester; N-Carbobenzoxy-L-phenylalanine vinyl ester; ethenyl N-[(benzyloxy)carbonyl]phenylalaninate
• CAS NO: 64187-42-4
• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.3585
• Mol File: 64187-42-4.mol
• Article Data: 2

Chemical Properties

• Refractive Index: 1.566
• CAS DataBase Reference: N-CARBOBENZOXY-L-PHENYLALANINE VINYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBOBENZOXY-L-PHENYLALANINE VINYL ESTER(64187-42-4)
• EPA Substance Registry System: N-CARBOBENZOXY-L-PHENYLALANINE VINYL ESTER(64187-42-4)

Safety Data

• Hazardous Substances Data: 64187-42-4(Hazardous Substances Data)

Usage

General Description

N-CARBOBENZOXY-L-PHENYLALANINE VINYL ESTER, also known as Z-Phe-VS, is a chemical compound used in the synthesis of peptides and proteins. It is a protected form of the amino acid phenylalanine, where the carboxylic acid group is masked as a benzyloxycarbonyl (Z) group. The vinyl ester function makes it a versatile reagent for the solid-phase synthesis of peptides, as it can be easily attached to solid supports and then cleaved and deprotected under mild conditions. N-CARBOBENZOXY-L-PHENYLALANINE VINYL ESTER is commonly used in the research and development of pharmaceuticals, as well as in the study of enzyme mechanisms, protein-protein interactions, and drug delivery systems. Due to its reactivity and stability, N-CARBOBENZOXY-L-PHENYLALANINE VINYL ESTER is an important tool in chemical biology and drug discovery.

Upstream product

• 108-05-4 vinyl acetate 
• 63-91-2 L-phenylalanine 
• 501-53-1 benzyl chloroformate 
• 1161-13-3 N-Cbz-L-Phe 

Relevant articles and documents

Regio- and Stereoselective Chan-Lam-Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines

Efficient and scalable Cu(II)-mediated enol esterification methodology of carboxylic acids from alkenyl boroxines and boronic acids is presented. The reaction shows a wide scope in aliphatic and aromatic carboxylic acids in combination with several alkenyl boroxines. In the case of 2-substituted alkenyl boroxines the double bond configuration was fully retained in the enol ester product. Also N-hydroxyimides and imides could be transformed in the respective amidooxy vinyl enol ethers and vinyl enamides. Finally, with the exception of methionine, all other 19 canonical amino acids showed their compatibility to give the enol esters in a stereoselective fashion. (Figure presented.).